JP2011500702A5

JP2011500702A5 -

Download PDF

Info

Publication number: JP2011500702A5
Authority: JP; Japan
Prior art keywords: phenyl; pyrazolo; alkyl; oxa; azabicyclo
Prior art date: 2008-10-15
Legal status : Withdrawn

Application number

JP2010530074A

Other languages

English (en)

Japanese (ja)

Other versions

JP2011500702A (ja

Filing date

2008-10-15

Publication date

2011-11-24

2008-10-15 Application filed filed Critical

2008-10-15 Priority claimed from PCT/US2008/079940 external-priority patent/WO2009052145A1/fr

2011-01-06 Publication of JP2011500702A publication Critical patent/JP2011500702A/ja

2011-11-24 Publication of JP2011500702A5 publication Critical patent/JP2011500702A5/ja

Status Withdrawn legal-status Critical Current

Links

-1 pyrazolopyrimidinyl group Chemical group 0.000 claims 210
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 90
125000001424 substituent group Chemical group 0.000 claims 89
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 84
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 78
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 71
125000003118 aryl group Chemical group 0.000 claims 57
125000001072 heteroaryl group Chemical group 0.000 claims 48
125000005843 halogen group Chemical group 0.000 claims 46
229910052736 halogen Inorganic materials 0.000 claims 43
150000002367 halogens Chemical class 0.000 claims 43
239000004202 carbamide Substances 0.000 claims 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 42
125000000217 alkyl group Chemical group 0.000 claims 39
229910052799 carbon Inorganic materials 0.000 claims 35
125000004432 carbon atom Chemical group C* 0.000 claims 35
125000002252 acyl group Chemical group 0.000 claims 31
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 31
150000001875 compounds Chemical class 0.000 claims 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 25
150000003839 salts Chemical class 0.000 claims 25
125000004430 oxygen atom Chemical group O* 0.000 claims 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 21
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 16
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 16
125000005530 alkylenedioxy group Chemical group 0.000 claims 15
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 13
125000000623 heterocyclic group Chemical group 0.000 claims 13
125000004415 heterocyclylalkyl group Chemical group 0.000 claims 11
229910052739 hydrogen Inorganic materials 0.000 claims 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
239000000203 mixture Substances 0.000 claims 10
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 9
125000003710 aryl alkyl group Chemical group 0.000 claims 9
239000001257 hydrogen Substances 0.000 claims 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
125000005431 alkyl carboxamide group Chemical group 0.000 claims 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 7
125000003341 7 membered heterocyclic group Chemical group 0.000 claims 6
125000005157 alkyl carboxy group Chemical group 0.000 claims 6
125000002619 bicyclic group Chemical group 0.000 claims 6
125000002911 monocyclic heterocycle group Chemical group 0.000 claims 6
229910052757 nitrogen Inorganic materials 0.000 claims 6
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 6
208000008839 Kidney Neoplasms Diseases 0.000 claims 5
206010028980 Neoplasm Diseases 0.000 claims 5
206010038389 Renal cancer Diseases 0.000 claims 5
125000004429 atom Chemical group 0.000 claims 5
201000011510 cancer Diseases 0.000 claims 5
201000010982 kidney cancer Diseases 0.000 claims 5
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
ULTTYPMRMMDONC-UHFFFAOYSA-N 5-[(2,5-dihydroxyphenyl)methyl-[(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C(=CC=CC=2)O)CC=2C(=CC=C(O)C=2)O)=C1 ULTTYPMRMMDONC-UHFFFAOYSA-N 0.000 claims 4
201000001320 Atherosclerosis Diseases 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
208000035475 disorder Diseases 0.000 claims 4
125000001188 haloalkyl group Chemical group 0.000 claims 4
125000001624 naphthyl group Chemical group 0.000 claims 4
QLHHRYZMBGPBJG-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-pyrazolo[3,4-d]pyrimidinyl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 QLHHRYZMBGPBJG-UHFFFAOYSA-N 0.000 claims 3
206010005003 Bladder cancer Diseases 0.000 claims 3
208000003174 Brain Neoplasms Diseases 0.000 claims 3
206010006187 Breast cancer Diseases 0.000 claims 3
208000026310 Breast neoplasm Diseases 0.000 claims 3
206010009944 Colon cancer Diseases 0.000 claims 3
206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
206010033128 Ovarian cancer Diseases 0.000 claims 3
206010061535 Ovarian neoplasm Diseases 0.000 claims 3
206010061902 Pancreatic neoplasm Diseases 0.000 claims 3
206010060862 Prostate cancer Diseases 0.000 claims 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
208000000453 Skin Neoplasms Diseases 0.000 claims 3
208000005718 Stomach Neoplasms Diseases 0.000 claims 3
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 3
208000002495 Uterine Neoplasms Diseases 0.000 claims 3
125000003545 alkoxy group Chemical group 0.000 claims 3
208000029742 colonic neoplasm Diseases 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
206010017758 gastric cancer Diseases 0.000 claims 3
208000032839 leukemia Diseases 0.000 claims 3
201000005202 lung cancer Diseases 0.000 claims 3
208000020816 lung neoplasm Diseases 0.000 claims 3
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 3
229960005419 nitrogen Drugs 0.000 claims 3
125000004433 nitrogen atom Chemical group N* 0.000 claims 3
201000002528 pancreatic cancer Diseases 0.000 claims 3
208000008443 pancreatic carcinoma Diseases 0.000 claims 3
201000000849 skin cancer Diseases 0.000 claims 3
201000011549 stomach cancer Diseases 0.000 claims 3
201000005112 urinary bladder cancer Diseases 0.000 claims 3
206010046766 uterine cancer Diseases 0.000 claims 3
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 2
SGRCPPFHVNOJSS-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3C4CCC3COC4)N=2)C=C1 SGRCPPFHVNOJSS-UHFFFAOYSA-N 0.000 claims 2
IZEKUGZAKDZVTI-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 IZEKUGZAKDZVTI-UHFFFAOYSA-N 0.000 claims 2
IJQBGHXJLLTXPZ-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(C4CCC5(CC4)OCCO5)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 IJQBGHXJLLTXPZ-UHFFFAOYSA-N 0.000 claims 2
CCJBBQMLLPYZTR-UHFFFAOYSA-N 1-[4-[1-(2-fluoroethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCF)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 CCJBBQMLLPYZTR-UHFFFAOYSA-N 0.000 claims 2
LQBQQAXIISEIGM-UHFFFAOYSA-N 1-[4-[1-(4-hydroxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(O)CC3)C2=N1 LQBQQAXIISEIGM-UHFFFAOYSA-N 0.000 claims 2
LDOKUGHHYHVRRK-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3C4CCC3COC4)N=2)C=C1 LDOKUGHHYHVRRK-UHFFFAOYSA-N 0.000 claims 2
KPSKKPDRNSLZRB-HOTGVXAUSA-N 1-cyclopropyl-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 KPSKKPDRNSLZRB-HOTGVXAUSA-N 0.000 claims 2
WRCVEGVPVQBJJW-UHFFFAOYSA-N 1-methyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(4-oxocyclohexyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(=O)CC3)C2=N1 WRCVEGVPVQBJJW-UHFFFAOYSA-N 0.000 claims 2
FZSZWXZCXGPTKY-UHFFFAOYSA-N 2-hydroxyethyl n-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCO)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC(F)(F)F)C2=N1 FZSZWXZCXGPTKY-UHFFFAOYSA-N 0.000 claims 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
208000020084 Bone disease Diseases 0.000 claims 2
RIWKUMGHZXCSPC-BZKVGYQJSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 RIWKUMGHZXCSPC-BZKVGYQJSA-N 0.000 claims 2
SYKXTQULDCRVJS-DPJKZYHESA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 SYKXTQULDCRVJS-DPJKZYHESA-N 0.000 claims 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims 2
206010012689 Diabetic retinopathy Diseases 0.000 claims 2
206010061218 Inflammation Diseases 0.000 claims 2
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 2
102000038030 PI3Ks Human genes 0.000 claims 2
108091007960 PI3Ks Proteins 0.000 claims 2
229930012538 Paclitaxel Natural products 0.000 claims 2
206010033645 Pancreatitis Diseases 0.000 claims 2
208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
201000004681 Psoriasis Diseases 0.000 claims 2
102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims 2
108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
125000003282 alkyl amino group Chemical group 0.000 claims 2
230000033115 angiogenesis Effects 0.000 claims 2
206010003246 arthritis Diseases 0.000 claims 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 2
229960004562 carboplatin Drugs 0.000 claims 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
229960004316 cisplatin Drugs 0.000 claims 2
125000004122 cyclic group Chemical group 0.000 claims 2
229960003901 dacarbazine Drugs 0.000 claims 2
229960004679 doxorubicin Drugs 0.000 claims 2
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 2
229960005420 etoposide Drugs 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
208000026278 immune system disease Diseases 0.000 claims 2
230000004054 inflammatory process Effects 0.000 claims 2
208000017169 kidney disease Diseases 0.000 claims 2
125000002950 monocyclic group Chemical group 0.000 claims 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
239000001301 oxygen Substances 0.000 claims 2
229960001592 paclitaxel Drugs 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
208000037803 restenosis Diseases 0.000 claims 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
VNRJYXRJFNRQRD-UHFFFAOYSA-N 1-(2-fluoroethyl)-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCF)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC(F)(F)F)C2=N1 VNRJYXRJFNRQRD-UHFFFAOYSA-N 0.000 claims 1
XBLBSXOUHOVQPA-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCO)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CCO)C2=N1 XBLBSXOUHOVQPA-UHFFFAOYSA-N 0.000 claims 1
FGCPYNHZGVJJLS-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC(F)(F)F)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 FGCPYNHZGVJJLS-UHFFFAOYSA-N 0.000 claims 1
BYGOEBYVFYSDGF-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC(F)(F)F)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 BYGOEBYVFYSDGF-UHFFFAOYSA-N 0.000 claims 1
LERUIIPTVXHCLN-GOTSBHOMSA-N 1-(4-morpholin-4-ylphenyl)-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 LERUIIPTVXHCLN-GOTSBHOMSA-N 0.000 claims 1
QKQRJVLKJZATTP-UHFFFAOYSA-N 1-(6-aminopyridin-3-yl)-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(N)N=C1 QKQRJVLKJZATTP-UHFFFAOYSA-N 0.000 claims 1
XAZGVAFGYQYKTL-UHFFFAOYSA-N 1-(6-morpholin-4-ylpyridin-3-yl)-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC(F)(F)F)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 XAZGVAFGYQYKTL-UHFFFAOYSA-N 0.000 claims 1
MONILLGMGZKJNK-UHFFFAOYSA-N 1-(6-morpholin-4-ylpyridin-3-yl)-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC(F)(F)F)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 MONILLGMGZKJNK-UHFFFAOYSA-N 0.000 claims 1
SNOHNXMOFHUTHI-SFTDATJTSA-N 1-(6-morpholin-4-ylpyridin-3-yl)-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 SNOHNXMOFHUTHI-SFTDATJTSA-N 0.000 claims 1
UCGFKGIOOUVIOP-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NCCN(C)C)C=C1 UCGFKGIOOUVIOP-UHFFFAOYSA-N 0.000 claims 1
OQALSGXMCNMPKF-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C)C2=N1 OQALSGXMCNMPKF-UHFFFAOYSA-N 0.000 claims 1
LYHVJYYVAHOIOZ-UHFFFAOYSA-N 1-[2-fluoro-4-[4-morpholin-4-yl-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound FC1=CC(C=2N=C3N(C4CCN(CC=5C=NC=CC=5)CC4)N=CC3=C(N3CCOCC3)N=2)=CC=C1NC(=O)NC1=CC=CN=C1 LYHVJYYVAHOIOZ-UHFFFAOYSA-N 0.000 claims 1
WOGPOVFUVILBEW-UHFFFAOYSA-N 1-[3-(dimethylamino)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound CN(C)C1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)=C1 WOGPOVFUVILBEW-UHFFFAOYSA-N 0.000 claims 1
ZTLYDMQLSAICDR-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCN(C)C)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C)C2=N1 ZTLYDMQLSAICDR-UHFFFAOYSA-N 0.000 claims 1
WAOKYKONZRCFJW-UHFFFAOYSA-N 1-[3-(hydroxymethyl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound OCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)=C1 WAOKYKONZRCFJW-UHFFFAOYSA-N 0.000 claims 1
UHVGWFGAZNCSFU-UHFFFAOYSA-N 1-[4-(2-hydroxyethoxy)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(OCCO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 UHVGWFGAZNCSFU-UHFFFAOYSA-N 0.000 claims 1
SAXVGQAUJGTTDG-UHFFFAOYSA-N 1-[4-(2-hydroxyethyl)phenyl]-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CCO)C=C1 SAXVGQAUJGTTDG-UHFFFAOYSA-N 0.000 claims 1
CKICPWIYCQZPMV-UHFFFAOYSA-N 1-[4-(2-hydroxyethyl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(CCO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3C4CCC3COC4)N=2)C=C1 CKICPWIYCQZPMV-UHFFFAOYSA-N 0.000 claims 1
MURNNMKLHXSXQC-UHFFFAOYSA-N 1-[4-(2-hydroxyethyl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(CCO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 MURNNMKLHXSXQC-UHFFFAOYSA-N 0.000 claims 1
ZYENMTFOLXJCOD-SFTDATJTSA-N 1-[4-(2-hydroxyethyl)phenyl]-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CCO)C=C1 ZYENMTFOLXJCOD-SFTDATJTSA-N 0.000 claims 1
RBVTXOAIFJHNSX-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(4-oxocyclohexyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(C4CCC(=O)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 RBVTXOAIFJHNSX-UHFFFAOYSA-N 0.000 claims 1
JCDUVMKYALYSCA-UHFFFAOYSA-N 1-[4-(4-methylpiperazin-1-yl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(4-propoxycyclohexyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CC(OCCC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 JCDUVMKYALYSCA-UHFFFAOYSA-N 0.000 claims 1
OGQRLNMAEQPGJF-UHFFFAOYSA-N 1-[4-(aminomethyl)phenyl]-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CN)C=C1 OGQRLNMAEQPGJF-UHFFFAOYSA-N 0.000 claims 1
ODSKIIXTBSXLGG-UHFFFAOYSA-N 1-[4-(aminomethyl)phenyl]-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CN)C=C1 ODSKIIXTBSXLGG-UHFFFAOYSA-N 0.000 claims 1
DBNVNMWEQKXYJD-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-3-[4-[1-(2-fluoroethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCF)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 DBNVNMWEQKXYJD-UHFFFAOYSA-N 0.000 claims 1
QDQFNJOBXNDVPS-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(C)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 QDQFNJOBXNDVPS-UHFFFAOYSA-N 0.000 claims 1
QRPPJJFFSLQATD-UHFFFAOYSA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(CO)=CC=4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 QRPPJJFFSLQATD-UHFFFAOYSA-N 0.000 claims 1
WXBFFWOJWOEYEC-UHFFFAOYSA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CO)C=C1 WXBFFWOJWOEYEC-UHFFFAOYSA-N 0.000 claims 1
BQEVGAXHNFPCTP-UHFFFAOYSA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(CO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3C4CCC3COC4)N=2)C=C1 BQEVGAXHNFPCTP-UHFFFAOYSA-N 0.000 claims 1
UKWDHIDULSJIRO-UHFFFAOYSA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(CO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 UKWDHIDULSJIRO-UHFFFAOYSA-N 0.000 claims 1
TZFINOAGXDAXAO-PMACEKPBSA-N 1-[4-(hydroxymethyl)phenyl]-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CO)C=C1 TZFINOAGXDAXAO-PMACEKPBSA-N 0.000 claims 1
MVWGPMLPVKVJOK-UHFFFAOYSA-N 1-[4-[(dimethylamino)methyl]phenyl]-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CN(C)C)C=C1 MVWGPMLPVKVJOK-UHFFFAOYSA-N 0.000 claims 1
XHNJXQFICQUYRG-UHFFFAOYSA-N 1-[4-[(dimethylamino)methyl]phenyl]-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CN(C)C)C=C1 XHNJXQFICQUYRG-UHFFFAOYSA-N 0.000 claims 1
HXNLDHXVQFPKQT-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-piperazin-1-ylphenyl)urea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCNCC1 HXNLDHXVQFPKQT-UHFFFAOYSA-N 0.000 claims 1
PDSIPAZDJRNBMR-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 PDSIPAZDJRNBMR-UHFFFAOYSA-N 0.000 claims 1
DZTUYZSGISMBPY-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(dimethylaminocarbamoyl)phenyl]urea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(=O)NN(C)C)C=C1 DZTUYZSGISMBPY-UHFFFAOYSA-N 0.000 claims 1
LQYGYODYVJISNS-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C(COC)COC)C2=N1 LQYGYODYVJISNS-UHFFFAOYSA-N 0.000 claims 1
NCUVYNDKUYLZDH-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C(COC)COC)C2=N1 NCUVYNDKUYLZDH-UHFFFAOYSA-N 0.000 claims 1
AYTHJCRLZQMVOO-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 AYTHJCRLZQMVOO-UHFFFAOYSA-N 0.000 claims 1
OAIVJKNKEIZODY-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 OAIVJKNKEIZODY-UHFFFAOYSA-N 0.000 claims 1
WNVWRJZTELCKHK-UHFFFAOYSA-N 1-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 WNVWRJZTELCKHK-UHFFFAOYSA-N 0.000 claims 1
LRLKPJBRGFJMKN-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(2-fluoroethyl)urea Chemical compound C1=CC(NC(=O)NCCF)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 LRLKPJBRGFJMKN-UHFFFAOYSA-N 0.000 claims 1
RSYAVMKTTXMNDN-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C1=CC(NC(=O)NCCO)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 RSYAVMKTTXMNDN-UHFFFAOYSA-N 0.000 claims 1
UQCOTILHWVGDGS-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC=C(C=2N=C3N(C4CCC5(CC4)OCCO5)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 UQCOTILHWVGDGS-UHFFFAOYSA-N 0.000 claims 1
YCAGJYZYGLPLRL-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 YCAGJYZYGLPLRL-UHFFFAOYSA-N 0.000 claims 1
VBYNNESGSHUXND-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound C=1C=C(C=2N=C3N(C4CCC5(CC4)OCCO5)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=CC=C1 VBYNNESGSHUXND-UHFFFAOYSA-N 0.000 claims 1
QYCBARGBDSITAT-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC(C=C1)=CC=C1C(N=C12)=NC(N3CC4CCC(O4)C3)=C1C=NN2C(CC1)CCC21OCCO2 QYCBARGBDSITAT-UHFFFAOYSA-N 0.000 claims 1
HGTXRLXWYACZEB-UHFFFAOYSA-N 1-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C3N(C4CCC5(CC4)OCCO5)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=NC=C1 HGTXRLXWYACZEB-UHFFFAOYSA-N 0.000 claims 1
QEZCXGHWXXLBFJ-UHFFFAOYSA-N 1-[4-[1-(1,5-dioxaspiro[5.5]undecan-9-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCCO4)C2=N1 QEZCXGHWXXLBFJ-UHFFFAOYSA-N 0.000 claims 1
GYOUBQRXSAHJQZ-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-morpholin-4-ylphenyl)urea Chemical compound C=1C=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 GYOUBQRXSAHJQZ-UHFFFAOYSA-N 0.000 claims 1
VLWYJTAQQPZAJL-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(6-morpholin-4-ylpyridin-3-yl)urea Chemical compound C=1C=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 VLWYJTAQQPZAJL-UHFFFAOYSA-N 0.000 claims 1
PYMQNCNMPKYHRR-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(2-hydroxyethyl)phenyl]urea Chemical compound C1=CC(CCO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 PYMQNCNMPKYHRR-UHFFFAOYSA-N 0.000 claims 1
ZLEWXVNORLUUGZ-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 ZLEWXVNORLUUGZ-UHFFFAOYSA-N 0.000 claims 1
XONAXDSGGBMHNG-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(hydroxymethyl)phenyl]urea Chemical compound C1=CC(CO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 XONAXDSGGBMHNG-UHFFFAOYSA-N 0.000 claims 1
UMLKHSOFLLPNQK-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-[2-(dimethylamino)ethoxy]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 UMLKHSOFLLPNQK-UHFFFAOYSA-N 0.000 claims 1
NFFZXYXQSLXDSU-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]urea Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 NFFZXYXQSLXDSU-UHFFFAOYSA-N 0.000 claims 1
YXYABVGBCDZUIA-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-cyclopropylurea Chemical compound C=1C=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1CC1 YXYABVGBCDZUIA-UHFFFAOYSA-N 0.000 claims 1
HJLBILJRSZZKJL-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CCC#N)C2=N1 HJLBILJRSZZKJL-UHFFFAOYSA-N 0.000 claims 1
YFADXJFERUTOIB-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=CN=C1 YFADXJFERUTOIB-UHFFFAOYSA-N 0.000 claims 1
RMJJDRYOMQIVJI-UHFFFAOYSA-N 1-[4-[1-(2-cyanoethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C3N(CCC#N)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=NC=C1 RMJJDRYOMQIVJI-UHFFFAOYSA-N 0.000 claims 1
SDRFXWMDVIHAMJ-UHFFFAOYSA-N 1-[4-[1-(2-fluoroethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-morpholin-4-ylphenyl)urea Chemical compound N1=C2N(CCF)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 SDRFXWMDVIHAMJ-UHFFFAOYSA-N 0.000 claims 1
LOKZPATYWMCLBT-UHFFFAOYSA-N 1-[4-[1-(2-fluoroethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(hydroxymethyl)phenyl]urea Chemical compound C1=CC(CO)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCF)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 LOKZPATYWMCLBT-UHFFFAOYSA-N 0.000 claims 1
MXKMECPPQGOGLO-UHFFFAOYSA-N 1-[4-[1-(2-fluoroethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CCF)C2=N1 MXKMECPPQGOGLO-UHFFFAOYSA-N 0.000 claims 1
IUCRTPCEYKAVPS-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-morpholin-4-ylphenyl)urea Chemical compound N1=C2N(CCO)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 IUCRTPCEYKAVPS-UHFFFAOYSA-N 0.000 claims 1
ZSUJALVCGZXBPH-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(6-morpholin-4-ylpyridin-3-yl)urea Chemical compound N1=C2N(CCO)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 ZSUJALVCGZXBPH-UHFFFAOYSA-N 0.000 claims 1
SIDHSIRXTZBQCO-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCO)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 SIDHSIRXTZBQCO-UHFFFAOYSA-N 0.000 claims 1
YYSOROXNNPPLPX-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(hydroxymethyl)phenyl]urea Chemical compound N1=C2N(CCO)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CO)C=C1 YYSOROXNNPPLPX-UHFFFAOYSA-N 0.000 claims 1
ZGURBBLDZYAUKZ-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]urea Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CCO)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 ZGURBBLDZYAUKZ-UHFFFAOYSA-N 0.000 claims 1
JLRPIYJFNRMCDO-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CCO)C2=N1 JLRPIYJFNRMCDO-UHFFFAOYSA-N 0.000 claims 1
CKZGHSVVDWPYPE-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound N1=C2N(CCO)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 CKZGHSVVDWPYPE-UHFFFAOYSA-N 0.000 claims 1
VQSNOIJAOVHRGF-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(CCO)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 VQSNOIJAOVHRGF-UHFFFAOYSA-N 0.000 claims 1
CAJRWBWOMGUTOF-UHFFFAOYSA-N 1-[4-[1-(2-hydroxyethyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(CCO)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 CAJRWBWOMGUTOF-UHFFFAOYSA-N 0.000 claims 1
RZERWDKPRCXFKM-UHFFFAOYSA-N 1-[4-[1-(4,4-dimethoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)(OC)OC)C2=N1 RZERWDKPRCXFKM-UHFFFAOYSA-N 0.000 claims 1
ZTEKLKSMMFAWQB-UHFFFAOYSA-N 1-[4-[1-(4-ethoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CC(OCC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 ZTEKLKSMMFAWQB-UHFFFAOYSA-N 0.000 claims 1
KJWBIIIGQKNAHW-UHFFFAOYSA-N 1-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-piperazin-1-ylphenyl)urea Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCNCC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 KJWBIIIGQKNAHW-UHFFFAOYSA-N 0.000 claims 1
SYKXTQULDCRVJS-UHFFFAOYSA-N 1-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 SYKXTQULDCRVJS-UHFFFAOYSA-N 0.000 claims 1
VATMREWLTYGLRS-UHFFFAOYSA-N 1-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]urea Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=NC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 VATMREWLTYGLRS-UHFFFAOYSA-N 0.000 claims 1
JSXSGODQMDFQIZ-UHFFFAOYSA-N 1-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=NC=CC=4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 JSXSGODQMDFQIZ-UHFFFAOYSA-N 0.000 claims 1
WYJZUOPYCRSROU-UHFFFAOYSA-N 1-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CN=CC=4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 WYJZUOPYCRSROU-UHFFFAOYSA-N 0.000 claims 1
ZZISZBHZKQPWHE-UHFFFAOYSA-N 1-[4-[1-[1-(2-methoxybenzoyl)piperidin-4-yl]-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC3)C(=O)C=3C(=CC=CC=3)OC)C2=N1 ZZISZBHZKQPWHE-UHFFFAOYSA-N 0.000 claims 1
JOYQWGOVTXHHHZ-UHFFFAOYSA-N 1-[4-[1-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound C1CN(C(=O)C(C)C)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC=CC=4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 JOYQWGOVTXHHHZ-UHFFFAOYSA-N 0.000 claims 1
AWUHGWHQDJVGFK-UHFFFAOYSA-N 1-[4-[1-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C1CN(C(=O)C(C)C)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=NC=CC=4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 AWUHGWHQDJVGFK-UHFFFAOYSA-N 0.000 claims 1
UPGZHLYKVZADRQ-UHFFFAOYSA-N 1-[4-[1-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C1CN(C(=O)C(C)C)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CN=CC=4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 UPGZHLYKVZADRQ-UHFFFAOYSA-N 0.000 claims 1
DCBCEXPXWXJOKW-UHFFFAOYSA-N 1-[4-[1-[1-(3-acetylbenzoyl)piperidin-4-yl]-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC3)C(=O)C=3C=C(C=CC=3)C(C)=O)C2=N1 DCBCEXPXWXJOKW-UHFFFAOYSA-N 0.000 claims 1
ALHMYQNCSUHAKI-UHFFFAOYSA-N 1-[4-[1-[1-[(6-bromopyridin-3-yl)methyl]piperidin-4-yl]-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC=4C=NC(Br)=CC=4)CC3)C2=N1 ALHMYQNCSUHAKI-UHFFFAOYSA-N 0.000 claims 1
AZZAJNGNFJIPRH-UHFFFAOYSA-N 1-[4-[1-[4-(2,2-dimethylhydrazinyl)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)NN(C)C)C2=N1 AZZAJNGNFJIPRH-UHFFFAOYSA-N 0.000 claims 1
GTWCTQSVXFCJEK-UHFFFAOYSA-N 1-[4-[1-[4-(2-hydroxyethylamino)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)NCCO)C2=N1 GTWCTQSVXFCJEK-UHFFFAOYSA-N 0.000 claims 1
GMSMKYNFVQSVJU-UHFFFAOYSA-N 1-[4-[1-[4-(4-methylpiperazin-1-yl)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound C1CN(C)CCN1C1CCC(N2C3=NC(=NC(=C3C=N2)N2CC3CCC(O3)C2)C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)CC1 GMSMKYNFVQSVJU-UHFFFAOYSA-N 0.000 claims 1
WYTADYJFVUAVOT-UHFFFAOYSA-N 1-[4-[1-[4-(4-methylpiperazin-1-yl)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C1CN(C)CCN1C1CCC(N2C3=NC(=NC(=C3C=N2)N2CC3CCC(O3)C2)C=2C=CC(NC(=O)NC=3C=NC=CC=3)=CC=2)CC1 WYTADYJFVUAVOT-UHFFFAOYSA-N 0.000 claims 1
UPBUHFORXUZSRN-UHFFFAOYSA-N 1-[4-[1-benzyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC=3C=CC=CC=3)C2=N1 UPBUHFORXUZSRN-UHFFFAOYSA-N 0.000 claims 1
NCKXTAXYVPUKBK-UHFFFAOYSA-N 1-[4-[1-benzyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC=3C=CC=CC=3)C2=N1 NCKXTAXYVPUKBK-UHFFFAOYSA-N 0.000 claims 1
NIHOWXYNRHYKFX-UHFFFAOYSA-N 1-[4-[1-benzyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C3N(CC=4C=CC=CC=4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=NC=C1 NIHOWXYNRHYKFX-UHFFFAOYSA-N 0.000 claims 1
JQEACQXIVNPOGS-UHFFFAOYSA-N 1-[4-[1-ethyl-3-(4-methylpiperazin-1-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C12=C(N3CC4CCC(O4)C3)N=C(C=3C=CC(NC(=O)NC)=CC=3)N=C2N(CC)N=C1N1CCN(C)CC1 JQEACQXIVNPOGS-UHFFFAOYSA-N 0.000 claims 1
RCHWHILZANOZHZ-UHFFFAOYSA-N 1-[4-[1-ethyl-3-[(4-methylpiperazin-1-yl)methyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C12=C(N3CC4CCC(O4)C3)N=C(C=3C=CC(NC(=O)NC)=CC=3)N=C2N(CC)N=C1CN1CCN(C)CC1 RCHWHILZANOZHZ-UHFFFAOYSA-N 0.000 claims 1
RSKRPMNJXANSOH-UHFFFAOYSA-N 1-[4-[1-ethyl-3-formyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound N1=C2N(CC)N=C(C=O)C2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NC)C=C1 RSKRPMNJXANSOH-UHFFFAOYSA-N 0.000 claims 1
ZKHQUVNCZZHVBY-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(2-pyrrolidin-1-ylethoxy)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OCCN1CCCC1 ZKHQUVNCZZHVBY-UHFFFAOYSA-N 0.000 claims 1
REAZWRUWNZTALY-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 REAZWRUWNZTALY-UHFFFAOYSA-N 0.000 claims 1
UFTUVGIEUVBLOO-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 UFTUVGIEUVBLOO-UHFFFAOYSA-N 0.000 claims 1
VZPAKKAWVXZJOO-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCN(C)CC1 VZPAKKAWVXZJOO-UHFFFAOYSA-N 0.000 claims 1
MKVPTYVBNXITMH-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C1=CC=C(NC(=O)NC)C=C1 MKVPTYVBNXITMH-UHFFFAOYSA-N 0.000 claims 1
ISKUMKPOLBEELU-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 ISKUMKPOLBEELU-UHFFFAOYSA-N 0.000 claims 1
XRIMHGBOUOLHBI-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 XRIMHGBOUOLHBI-UHFFFAOYSA-N 0.000 claims 1
AWTBEQWBRRKGKB-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 AWTBEQWBRRKGKB-UHFFFAOYSA-N 0.000 claims 1
FFSFJYJABLLMKY-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(1-methylpiperidin-4-yl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CCN(C)CC1 FFSFJYJABLLMKY-UHFFFAOYSA-N 0.000 claims 1
PTVAHFLJYTVLPN-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(2-fluoroethyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NCCF)C=C1 PTVAHFLJYTVLPN-UHFFFAOYSA-N 0.000 claims 1
SBGTVFMGDAHBNE-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NCCO)C=C1 SBGTVFMGDAHBNE-UHFFFAOYSA-N 0.000 claims 1
UBTJIBVOHICGEY-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NCCN1CCOCC1 UBTJIBVOHICGEY-UHFFFAOYSA-N 0.000 claims 1
DDPCJPFCPSGJOG-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-methoxyphenyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC)C=C1 DDPCJPFCPSGJOG-UHFFFAOYSA-N 0.000 claims 1
YFUIEEMMAVGYTI-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-methylphenyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C)C=C1 YFUIEEMMAVGYTI-UHFFFAOYSA-N 0.000 claims 1
MHEFFNLOVMOWPU-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-morpholin-4-ylphenyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 MHEFFNLOVMOWPU-UHFFFAOYSA-N 0.000 claims 1
OIZVMINJTWHORX-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-piperazin-1-ylphenyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCNCC1 OIZVMINJTWHORX-UHFFFAOYSA-N 0.000 claims 1
WLTGGZJCDZMNBZ-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-pyrrolidin-1-ylphenyl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCCC1 WLTGGZJCDZMNBZ-UHFFFAOYSA-N 0.000 claims 1
RCWCYHYCUNPFSO-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(6-morpholin-4-ylpyridin-3-yl)urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 RCWCYHYCUNPFSO-UHFFFAOYSA-N 0.000 claims 1
WTXTUPLZVSNWLB-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[(1-methylpiperidin-4-yl)methyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NCC1CCN(C)CC1 WTXTUPLZVSNWLB-UHFFFAOYSA-N 0.000 claims 1
XGIZKKOTRRCGLQ-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NCC(=O)N1CCN(C)CC1 XGIZKKOTRRCGLQ-UHFFFAOYSA-N 0.000 claims 1
CXNZGMDFFGLRLY-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NCCN1CCN(C)CC1 CXNZGMDFFGLRLY-UHFFFAOYSA-N 0.000 claims 1
KJAJGXINFQAKHZ-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[2-(methylamino)ethyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NCCNC)C=C1 KJAJGXINFQAKHZ-UHFFFAOYSA-N 0.000 claims 1
UTMQDJIIJVAEMU-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NCCC(=O)N1CCN(C)CC1 UTMQDJIIJVAEMU-UHFFFAOYSA-N 0.000 claims 1
NEMWIAVOKJWJCS-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[3-(methylamino)propyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NCCCNC)C=C1 NEMWIAVOKJWJCS-UHFFFAOYSA-N 0.000 claims 1
JQGIMHVWTOXCTP-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(2-hydroxyethoxy)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OCCO)C=C1 JQGIMHVWTOXCTP-UHFFFAOYSA-N 0.000 claims 1
ATLHTKSZGMIXLX-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(2-hydroxyethyl)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CCO)C=C1 ATLHTKSZGMIXLX-UHFFFAOYSA-N 0.000 claims 1
KYUFDBIYWRJMMF-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCN(C)CC1 KYUFDBIYWRJMMF-UHFFFAOYSA-N 0.000 claims 1
HNNBGLRKAYUYCE-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(hydroxymethyl)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(CO)C=C1 HNNBGLRKAYUYCE-UHFFFAOYSA-N 0.000 claims 1
JGCLMPLLEOAPAC-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(pyrrolidin-1-ylmethyl)phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCCC1 JGCLMPLLEOAPAC-UHFFFAOYSA-N 0.000 claims 1
FTRSKAKWKUDZKU-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 FTRSKAKWKUDZKU-UHFFFAOYSA-N 0.000 claims 1
YDFWAAMONNHYQX-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(2-hydroxyethoxy)pyridin-3-yl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OCCO)N=C1 YDFWAAMONNHYQX-UHFFFAOYSA-N 0.000 claims 1
LSPYTXAQSKEIJE-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(2-morpholin-4-ylethoxy)pyridin-3-yl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1OCCN1CCOCC1 LSPYTXAQSKEIJE-UHFFFAOYSA-N 0.000 claims 1
VKSCSFHLPAAEGS-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCN(C)CC1 VKSCSFHLPAAEGS-UHFFFAOYSA-N 0.000 claims 1
ARKRGLDVMPXTLI-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(methylamino)pyridin-3-yl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(NC)N=C1 ARKRGLDVMPXTLI-UHFFFAOYSA-N 0.000 claims 1
DPFONBIFXAOZIL-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NC)C=C1 DPFONBIFXAOZIL-UHFFFAOYSA-N 0.000 claims 1
ADCADUHNSKXDGZ-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 ADCADUHNSKXDGZ-UHFFFAOYSA-N 0.000 claims 1
AUXKCHHCFDLRBV-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 AUXKCHHCFDLRBV-UHFFFAOYSA-N 0.000 claims 1
OIUUQUNTDMZTRN-UHFFFAOYSA-N 1-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 OIUUQUNTDMZTRN-UHFFFAOYSA-N 0.000 claims 1
UGUVKBXJXFNVFA-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-methylsulfonylphenyl)urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(S(C)(=O)=O)C=C1 UGUVKBXJXFNVFA-UHFFFAOYSA-N 0.000 claims 1
HOYKWWOQTAMPCR-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-morpholin-4-ylphenyl)urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 HOYKWWOQTAMPCR-UHFFFAOYSA-N 0.000 claims 1
UFQYFACWJGZKBQ-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(6-morpholin-4-ylpyridin-3-yl)urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=N1)=CC=C1N1CCOCC1 UFQYFACWJGZKBQ-UHFFFAOYSA-N 0.000 claims 1
IEWKJELUKQVDKG-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(2-piperidin-1-ylethylsulfonyl)phenyl]urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1S(=O)(=O)CCN1CCCCC1 IEWKJELUKQVDKG-UHFFFAOYSA-N 0.000 claims 1
YQGJXFKRKDSFOO-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[4-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(C)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 YQGJXFKRKDSFOO-UHFFFAOYSA-N 0.000 claims 1
POANRMCBZWELLZ-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]urea Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(C)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 POANRMCBZWELLZ-UHFFFAOYSA-N 0.000 claims 1
GIQRDHHCACLCDO-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 GIQRDHHCACLCDO-UHFFFAOYSA-N 0.000 claims 1
MAMRCWLIONFVJH-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 MAMRCWLIONFVJH-UHFFFAOYSA-N 0.000 claims 1
GHDIKFLCCIGIID-UHFFFAOYSA-N 1-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 GHDIKFLCCIGIID-UHFFFAOYSA-N 0.000 claims 1
SUAHTQMBINZOHP-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OCCN(C)C)C=C1 SUAHTQMBINZOHP-UHFFFAOYSA-N 0.000 claims 1
PZMZFBMKDSXMES-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(OCCN(C)C)C=C1 PZMZFBMKDSXMES-UHFFFAOYSA-N 0.000 claims 1
OSGQEEGQMFEXAB-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3C4COCC3COC4)N=2)C=C1 OSGQEEGQMFEXAB-UHFFFAOYSA-N 0.000 claims 1
OCKKJHVJQPASQW-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-3-[4-[4-(3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3C4CNCC3COC4)N=2)C=C1 OCKKJHVJQPASQW-UHFFFAOYSA-N 0.000 claims 1
FBZDNEIODKLVDN-UHFFFAOYSA-N 1-[4-[3-(1,2-dihydroxyethyl)-1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound N1=C2N(CC)N=C(C(O)CO)C2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NC)C=C1 FBZDNEIODKLVDN-UHFFFAOYSA-N 0.000 claims 1
GWQJCRNIPKKUFO-UHFFFAOYSA-N 1-[4-[3-bromo-1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound N1=C2N(CC)N=C(Br)C2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NC)C=C1 GWQJCRNIPKKUFO-UHFFFAOYSA-N 0.000 claims 1
JEJCRWFEOZVUSQ-UHFFFAOYSA-N 1-[4-[3-ethenyl-1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound N1=C2N(CC)N=C(C=C)C2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)NC)C=C1 JEJCRWFEOZVUSQ-UHFFFAOYSA-N 0.000 claims 1
IDJREHHFYLMPLX-UHFFFAOYSA-N 1-[4-[4-(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2C3COCC2COC3)=C(C=NN2CC(F)(F)F)C2=N1 IDJREHHFYLMPLX-UHFFFAOYSA-N 0.000 claims 1
XFXAJYFCPLMACD-UHFFFAOYSA-N 1-[4-[4-(3-acetyl-9-oxa-3,7-diazabicyclo[3.3.1]nonan-7-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C1C(O2)CN(C(=O)C)CC2CN1C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 XFXAJYFCPLMACD-UHFFFAOYSA-N 0.000 claims 1
PRMNLVQQVAFCRJ-UHFFFAOYSA-N 1-[4-[4-(6,8-dioxa-3-azabicyclo[3.2.1]octan-3-yl)-1-methylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3OCC(O3)C2)=C(C=NN2C)C2=N1 PRMNLVQQVAFCRJ-UHFFFAOYSA-N 0.000 claims 1
NQESUZMBIJHCOM-UHFFFAOYSA-N 1-[4-[4-(6,8-dioxa-3-azabicyclo[3.2.1]octan-3-yl)-1-methylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(C)N=CC2=C(N2CC3OCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 NQESUZMBIJHCOM-UHFFFAOYSA-N 0.000 claims 1
ZWBNLUMFYUXGMK-UHFFFAOYSA-N 1-[4-[4-(6-hydroxy-3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2C3C(O)CC2COC3)=C(C=NN2CC(F)(F)F)C2=N1 ZWBNLUMFYUXGMK-UHFFFAOYSA-N 0.000 claims 1
LVOMIMOWTKHHCX-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(4-pyrrolidin-1-ylcyclohexyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC(C=C1)=CC=C1C(N=C12)=NC(N3CC4CCC(O4)C3)=C1C=NN2C(CC1)CCC1N1CCCC1 LVOMIMOWTKHHCX-UHFFFAOYSA-N 0.000 claims 1
YXLIUTQVEMJFQR-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound C=1C=C(C=2N=C3N(C4CCN(CC=5C=NC=CC=5)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=CC=C1 YXLIUTQVEMJFQR-UHFFFAOYSA-N 0.000 claims 1
LCHYMODHMGJDEG-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=CN=CC=1NC(=O)NC(C=C1)=CC=C1C(N=C12)=NC(N3CC4CCC(O4)C3)=C1C=NN2C(CC1)CCN1CC1=CC=CN=C1 LCHYMODHMGJDEG-UHFFFAOYSA-N 0.000 claims 1
YHOJJHQLBNYACI-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C3N(C4CCN(CC=5C=NC=CC=5)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=NC=C1 YHOJJHQLBNYACI-UHFFFAOYSA-N 0.000 claims 1
IEUHFTUDDSBTPZ-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-piperidin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound C=1C=C(C=2N=C3N(C4CCNCC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=CC=C1 IEUHFTUDDSBTPZ-UHFFFAOYSA-N 0.000 claims 1
JXMJEHGYAODUJF-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound N1=C2N(C(C)C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 JXMJEHGYAODUJF-UHFFFAOYSA-N 0.000 claims 1
QGMKUMYDPUQICJ-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound N1=C2N(C(C)C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 QGMKUMYDPUQICJ-UHFFFAOYSA-N 0.000 claims 1
IYEVLTXSGWCTAD-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(C(C)C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 IYEVLTXSGWCTAD-UHFFFAOYSA-N 0.000 claims 1
BRFGDDGSUBMDBH-UHFFFAOYSA-N 1-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1h-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C=1C=C(C=2N=C3NN=CC3=C(N3CC4CCC(O4)C3)N=2)C=CC=1NC(=O)NC1=CC=CN=C1 BRFGDDGSUBMDBH-UHFFFAOYSA-N 0.000 claims 1
YCEUUXAHOHKAHA-UHFFFAOYSA-N 1-[4-[4-(9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound N1=C2N(CC(F)(F)F)N=CC2=C(N2CC3CNCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 YCEUUXAHOHKAHA-UHFFFAOYSA-N 0.000 claims 1
RJGLKNSJUHURHU-QZTJIDSGSA-N 1-[4-[4-[(1r,4r)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C([C@@]1(OC[C@@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 RJGLKNSJUHURHU-QZTJIDSGSA-N 0.000 claims 1
KCNLNGDCXVYHOV-GOTSBHOMSA-N 1-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-(4-piperazin-1-ylphenyl)urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1N1CCNCC1 KCNLNGDCXVYHOV-GOTSBHOMSA-N 0.000 claims 1
RJGLKNSJUHURHU-ROUUACIJSA-N 1-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CN=C1 RJGLKNSJUHURHU-ROUUACIJSA-N 0.000 claims 1
MTIARLQVNAAYGF-UHFFFAOYSA-N 1-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(CC(F)(F)F)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 MTIARLQVNAAYGF-UHFFFAOYSA-N 0.000 claims 1
ZRLCNRCZZGRZFX-UHFFFAOYSA-N 1-[6-(dimethylamino)pyridin-3-yl]-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1=CC=C(N(C)C)N=C1 ZRLCNRCZZGRZFX-UHFFFAOYSA-N 0.000 claims 1
102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 claims 1
MFTYVNINGHVIAZ-UHFFFAOYSA-N 1-cyclobutyl-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1CCC1 MFTYVNINGHVIAZ-UHFFFAOYSA-N 0.000 claims 1
MMBMMCNNHSRFHN-UHFFFAOYSA-N 1-cyclobutyl-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CCC1 MMBMMCNNHSRFHN-UHFFFAOYSA-N 0.000 claims 1
YZGNQXOACOIHPE-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CCCCC1 YZGNQXOACOIHPE-UHFFFAOYSA-N 0.000 claims 1
FZMBSBWLFYCGKO-UHFFFAOYSA-N 1-cyclopentyl-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1CCCC1 FZMBSBWLFYCGKO-UHFFFAOYSA-N 0.000 claims 1
QYDXAFZEYDCSCJ-UHFFFAOYSA-N 1-cyclopentyl-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CCCC1 QYDXAFZEYDCSCJ-UHFFFAOYSA-N 0.000 claims 1
WNUHYBGWXNXCSK-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 WNUHYBGWXNXCSK-UHFFFAOYSA-N 0.000 claims 1
ZTNUCBXTEODPOV-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CN(C(=O)C(C)C)CCC1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 ZTNUCBXTEODPOV-UHFFFAOYSA-N 0.000 claims 1
RTVWGFBQAKFHOF-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-[2-(dimethylamino)ethyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CCN(C)C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 RTVWGFBQAKFHOF-UHFFFAOYSA-N 0.000 claims 1
XYMCMQNRZAYJFU-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-[4-(4-methylpiperazin-1-yl)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1CCC(N2C3=NC(=NC(=C3C=N2)N2CC3CCC(O3)C2)C=2C=CC(NC(=O)NC3CC3)=CC=2)CC1 XYMCMQNRZAYJFU-UHFFFAOYSA-N 0.000 claims 1
MNULAUCQBUJRSU-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2C3CCC2COC3)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 MNULAUCQBUJRSU-UHFFFAOYSA-N 0.000 claims 1
KCCHNABARLWHHJ-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 KCCHNABARLWHHJ-UHFFFAOYSA-N 0.000 claims 1
XCQIYNDFAUQWDO-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 XCQIYNDFAUQWDO-UHFFFAOYSA-N 0.000 claims 1
QXXPDHWWQICWNI-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(CC(F)(F)F)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 QXXPDHWWQICWNI-UHFFFAOYSA-N 0.000 claims 1
ZHQTWCWSCZLANL-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound N1=C2N(C(C)C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC1CC1 ZHQTWCWSCZLANL-UHFFFAOYSA-N 0.000 claims 1
KPSKKPDRNSLZRB-HZPDHXFCSA-N 1-cyclopropyl-3-[4-[4-[(1r,4r)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@@]1(OC[C@@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 KPSKKPDRNSLZRB-HZPDHXFCSA-N 0.000 claims 1
FDLVQFRXPKVPPN-UHFFFAOYSA-N 1-ethyl-3-[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)OC)C2=N1 FDLVQFRXPKVPPN-UHFFFAOYSA-N 0.000 claims 1
CUNNEAHMWONEIJ-UHFFFAOYSA-N 1-ethyl-3-[4-[1-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC3)C(=O)C(C)C)C2=N1 CUNNEAHMWONEIJ-UHFFFAOYSA-N 0.000 claims 1
ZXXBGPFLOBZGTR-UHFFFAOYSA-N 1-ethyl-3-[4-[1-[4-(4-methylpiperazin-1-yl)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)N3CCN(C)CC3)C2=N1 ZXXBGPFLOBZGTR-UHFFFAOYSA-N 0.000 claims 1
FZZHKLCKAGUQLD-UHFFFAOYSA-N 1-ethyl-3-[4-[1-ethyl-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2C3CCC2COC3)=C(C=NN2CC)C2=N1 FZZHKLCKAGUQLD-UHFFFAOYSA-N 0.000 claims 1
DZCKHQBHPTXSEC-UHFFFAOYSA-N 1-ethyl-3-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC)C2=N1 DZCKHQBHPTXSEC-UHFFFAOYSA-N 0.000 claims 1
KQLINRHJAKDXAU-UHFFFAOYSA-N 1-ethyl-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C)C2=N1 KQLINRHJAKDXAU-UHFFFAOYSA-N 0.000 claims 1
VBYFBAFSCCDPJJ-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC(F)(F)F)C2=N1 VBYFBAFSCCDPJJ-UHFFFAOYSA-N 0.000 claims 1
BMNJFVMKTJUWFA-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC=4C=NC=CC=4)CC3)C2=N1 BMNJFVMKTJUWFA-UHFFFAOYSA-N 0.000 claims 1
PBSYYSWMQXZEEP-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C(C)C)C2=N1 PBSYYSWMQXZEEP-UHFFFAOYSA-N 0.000 claims 1
IFCDUAOURDQOHG-UHFFFAOYSA-N 1-methyl-3-[4-[1-[1-(2-methylpropanoyl)piperidin-4-yl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC3)C(=O)C(C)C)C2=N1 IFCDUAOURDQOHG-UHFFFAOYSA-N 0.000 claims 1
IWBFIWBQNCLJEG-UHFFFAOYSA-N 1-methyl-3-[4-[1-[1-(2-methylpyridine-3-carbonyl)piperidin-4-yl]-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC3)C(=O)C=3C(=NC=CC=3)C)C2=N1 IWBFIWBQNCLJEG-UHFFFAOYSA-N 0.000 claims 1
QFUOOPGLNQIHSJ-UHFFFAOYSA-N 1-methyl-3-[4-[1-[1-(4-methylpyridine-3-carbonyl)piperidin-4-yl]-4-morpholin-4-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC3)C(=O)C=3C(=CC=NC=3)C)C2=N1 QFUOOPGLNQIHSJ-UHFFFAOYSA-N 0.000 claims 1
OCEMYPICVNLEAL-UHFFFAOYSA-N 1-methyl-3-[4-[1-[4-(4-methylpiperazin-1-yl)cyclohexyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)N3CCN(C)CC3)C2=N1 OCEMYPICVNLEAL-UHFFFAOYSA-N 0.000 claims 1
APYPCVRCUBVUDW-UHFFFAOYSA-N 1-methyl-3-[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C)C2=N1 APYPCVRCUBVUDW-UHFFFAOYSA-N 0.000 claims 1
PTCNGQVRIOAUFG-UHFFFAOYSA-N 1-methyl-3-[4-[4-(3-oxa-7,9-diazabicyclo[3.3.1]nonan-9-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2C3CNCC2COC3)=C(C=NN2CC(F)(F)F)C2=N1 PTCNGQVRIOAUFG-UHFFFAOYSA-N 0.000 claims 1
YKHJGTINLIVMSH-UHFFFAOYSA-N 1-methyl-3-[4-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2C3CCC2COC3)=C(C=NN2CC(F)(F)F)C2=N1 YKHJGTINLIVMSH-UHFFFAOYSA-N 0.000 claims 1
LHKWYVSHKLEEJS-UHFFFAOYSA-N 1-methyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC(F)(F)F)C2=N1 LHKWYVSHKLEEJS-UHFFFAOYSA-N 0.000 claims 1
QUMQCWMSCSDDMX-UHFFFAOYSA-N 1-methyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(4-pyrrolidin-1-ylcyclohexyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC(CC3)N3CCCC3)C2=N1 QUMQCWMSCSDDMX-UHFFFAOYSA-N 0.000 claims 1
DLOCQUMLEMAOPE-UHFFFAOYSA-N 1-methyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC(F)(F)F)CC3)C2=N1 DLOCQUMLEMAOPE-UHFFFAOYSA-N 0.000 claims 1
WOZYVVSCKUPLTE-UHFFFAOYSA-N 1-methyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC=4C=NC=CC=4)CC3)C2=N1 WOZYVVSCKUPLTE-UHFFFAOYSA-N 0.000 claims 1
QAQUVBOSSUCOMU-UHFFFAOYSA-N 1-methyl-3-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C(C)C)C2=N1 QAQUVBOSSUCOMU-UHFFFAOYSA-N 0.000 claims 1
GBTSKWANNRXPIL-ZIAGYGMSSA-N 1-methyl-3-[4-[4-[(1r,4r)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@@]1(OC[C@@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C1=CC=C(NC(=O)NC)C=C1 GBTSKWANNRXPIL-ZIAGYGMSSA-N 0.000 claims 1
GBTSKWANNRXPIL-KBPBESRZSA-N 1-methyl-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C1=CC=C(NC(=O)NC)C=C1 GBTSKWANNRXPIL-KBPBESRZSA-N 0.000 claims 1
RYTSQRBTBIDDPO-UHFFFAOYSA-N 1-methyl-3-[4-[4-morpholin-4-yl-1-[1-(pyridin-2-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC=4N=CC=CC=4)CC3)C2=N1 RYTSQRBTBIDDPO-UHFFFAOYSA-N 0.000 claims 1
YWWSGKYAMVMIMB-UHFFFAOYSA-N 1-methyl-3-[4-[4-morpholin-4-yl-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=C(C=NN2C3CCN(CC=4C=NC=CC=4)CC3)C2=N1 YWWSGKYAMVMIMB-UHFFFAOYSA-N 0.000 claims 1
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 1
UNBCXQQDKMJLJR-UHFFFAOYSA-N 2-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]anilino]ethanol Chemical compound C1=CC(NCCO)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 UNBCXQQDKMJLJR-UHFFFAOYSA-N 0.000 claims 1
NAUAFJAQVSIKKQ-UHFFFAOYSA-N 2-[6-(4-aminophenyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-1-yl]ethanol Chemical compound C1=CC(N)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CCO)C2=N1 NAUAFJAQVSIKKQ-UHFFFAOYSA-N 0.000 claims 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
FGMZJCUDMPVZPL-UHFFFAOYSA-N 2-fluoroethyl n-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCF)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 FGMZJCUDMPVZPL-UHFFFAOYSA-N 0.000 claims 1
DLAORXOIJUEBDN-GJZGRUSLSA-N 2-hydroxyethyl N-[4-[4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound [C@@H]12OC[C@@H](N(C1)C1=C3C(=NC(=N1)C1=CC=C(C=C1)NC(OCCO)=O)N(N=C3)CC(F)(F)F)C2 DLAORXOIJUEBDN-GJZGRUSLSA-N 0.000 claims 1
JVQGMMPEGNLKNE-UHFFFAOYSA-N 2-hydroxyethyl n-[4-[1-(1,3-dimethoxypropan-2-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound N1=C2N(C(COC)COC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)OCCO)C=C1 JVQGMMPEGNLKNE-UHFFFAOYSA-N 0.000 claims 1
DLAORXOIJUEBDN-HUUCEWRRSA-N 2-hydroxyethyl n-[4-[4-[(1r,4r)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCO)=CC=C1C1=NC(N2[C@@H]3C[C@@H](OC3)C2)=C(C=NN2CC(F)(F)F)C2=N1 DLAORXOIJUEBDN-HUUCEWRRSA-N 0.000 claims 1
JMQPGBQRHYWIGC-UHFFFAOYSA-N 3-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenol Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=CC(O)=C1 JMQPGBQRHYWIGC-UHFFFAOYSA-N 0.000 claims 1
GVUAZTSFHDKFPH-UHFFFAOYSA-N 3-[1-ethyl-6-(1h-indol-5-yl)pyrazolo[3,4-d]pyrimidin-4-yl]-8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1C(O2)CCC2CN1C1=C2C=NN(CC)C2=NC(C=2C=C3C=CNC3=CC=2)=N1 GVUAZTSFHDKFPH-UHFFFAOYSA-N 0.000 claims 1
CMNWKFRKWPPELQ-UHFFFAOYSA-N 3-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenol Chemical compound N1=C2N(C)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=CC(O)=C1 CMNWKFRKWPPELQ-UHFFFAOYSA-N 0.000 claims 1
IESRDZAZMXANTH-UHFFFAOYSA-N 3-[4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3N(C=4C=CC=CC=4)N=CC3=C(N3C4CCC3COC4)N=2)=C1 IESRDZAZMXANTH-UHFFFAOYSA-N 0.000 claims 1
XHIBKBRCVQLOJC-UHFFFAOYSA-N 3-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3N(C=4C=CC=CC=4)N=CC3=C(N3CC4CCC(O4)C3)N=2)=C1 XHIBKBRCVQLOJC-UHFFFAOYSA-N 0.000 claims 1
RXVOHEFEHZLXAX-WMZOPIPTSA-N 3-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl]phenol Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1C=N2)=NC(C=3C=C(O)C=CC=3)=NC=1N2C1=CC=CC=C1 RXVOHEFEHZLXAX-WMZOPIPTSA-N 0.000 claims 1
LWPJUOKZTSXFGN-UHFFFAOYSA-N 3-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=C(C=2N=C3N(C4CCC5(CC4)OCCO5)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 LWPJUOKZTSXFGN-UHFFFAOYSA-N 0.000 claims 1
JWHDDZUUGOBHNV-UHFFFAOYSA-N 3-[6-(1h-indol-5-yl)-1-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrazolo[3,4-d]pyrimidin-4-yl]-8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1CC(N2C3=NC(=NC(=C3C=N2)N2CC3CCC(O3)C2)C=2C=C3C=CNC3=CC=2)CCN1CC1=CC=CN=C1 JWHDDZUUGOBHNV-UHFFFAOYSA-N 0.000 claims 1
AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 1
IVPDYDHTKYINMP-UHFFFAOYSA-N 4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 IVPDYDHTKYINMP-UHFFFAOYSA-N 0.000 claims 1
YTUFNDUAVVBLJJ-UHFFFAOYSA-N 4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-6-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2CC(F)(F)F)C2=N1 YTUFNDUAVVBLJJ-UHFFFAOYSA-N 0.000 claims 1
GLKBJTKFTXGDAJ-UHFFFAOYSA-N 4-[[1-(1-benzylpiperidin-4-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]amino]phenol Chemical compound C1=CC(O)=CC=C1NC1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC=4C=CC=CC=4)CC3)C2=N1 GLKBJTKFTXGDAJ-UHFFFAOYSA-N 0.000 claims 1
CPEJHBIMMNNRFZ-UHFFFAOYSA-N 4-[[4-[1-(4-methoxycyclohexyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamoylamino]-n-pyrrolidin-1-ylbenzamide Chemical compound C1CC(OC)CCC1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)C(=O)NN4CCCC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 CPEJHBIMMNNRFZ-UHFFFAOYSA-N 0.000 claims 1
QWUNRYMMAGVRMS-UHFFFAOYSA-N 4-[[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamoylamino]-n-pyrrolidin-1-ylbenzamide Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1C(=O)NN1CCCC1 QWUNRYMMAGVRMS-UHFFFAOYSA-N 0.000 claims 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims 1
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 1
108010024976 Asparaginase Proteins 0.000 claims 1
108010006654 Bleomycin Proteins 0.000 claims 1
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
GLPFIJPUIPBENR-RQDRIDHYSA-N C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N([C@@H]4CC[C@@H](O)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N([C@@H]4CC[C@@H](O)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 GLPFIJPUIPBENR-RQDRIDHYSA-N 0.000 claims 1
GLPFIJPUIPBENR-WNUBJLNHSA-N C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N([C@H]4CC[C@@H](O)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N([C@H]4CC[C@@H](O)CC4)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 GLPFIJPUIPBENR-WNUBJLNHSA-N 0.000 claims 1
QRFAFGCAVNGXKY-IJDVVPKISA-N C1C[C@@H](O)CC[C@@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 Chemical compound C1C[C@@H](O)CC[C@@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 QRFAFGCAVNGXKY-IJDVVPKISA-N 0.000 claims 1
QRFAFGCAVNGXKY-FDRBHKFBSA-N C1C[C@@H](O)CC[C@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 Chemical compound C1C[C@@H](O)CC[C@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 QRFAFGCAVNGXKY-FDRBHKFBSA-N 0.000 claims 1
RIWKUMGHZXCSPC-OIRDZHBESA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=CC(NC(=O)NC4CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 RIWKUMGHZXCSPC-OIRDZHBESA-N 0.000 claims 1
SYKXTQULDCRVJS-DTVRLADWSA-N C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 Chemical compound C1C[C@@H](OC)CC[C@H]1N1C2=NC(C=3C=CC(NC(=O)NC=4C=CC(=CC=4)N4CCN(C)CC4)=CC=3)=NC(N3CC4CCC(O4)C3)=C2C=N1 SYKXTQULDCRVJS-DTVRLADWSA-N 0.000 claims 1
GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 1
GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 1
229940123780 DNA topoisomerase I inhibitor Drugs 0.000 claims 1
108010092160 Dactinomycin Proteins 0.000 claims 1
241000790917 Dioxys <bee> Species 0.000 claims 1
HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
108010072051 Glatiramer Acetate Proteins 0.000 claims 1
MCAHMSDENAOJFZ-UHFFFAOYSA-N Herbimycin A Natural products N1C(=O)C(C)=CC=CC(OC)C(OC(N)=O)C(C)=CC(C)C(OC)C(OC)CC(C)C(OC)C2=CC(=O)C=C1C2=O MCAHMSDENAOJFZ-UHFFFAOYSA-N 0.000 claims 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims 1
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims 1
108010005716 Interferon beta-1a Proteins 0.000 claims 1
108010005714 Interferon beta-1b Proteins 0.000 claims 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 claims 1
229930192392 Mitomycin Natural products 0.000 claims 1
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 1
FAUNBOBDFJICCL-XVJQKTIWSA-N N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)N[C@@H]1CC[C@H](N)CC1 Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)N[C@@H]1CC[C@H](N)CC1 FAUNBOBDFJICCL-XVJQKTIWSA-N 0.000 claims 1
FAUNBOBDFJICCL-SNXBXODESA-N N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)N[C@H]1CC[C@H](N)CC1 Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C(C=C1)=CC=C1NC(=O)N[C@H]1CC[C@H](N)CC1 FAUNBOBDFJICCL-SNXBXODESA-N 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
239000000365 Topoisomerase I Inhibitor Substances 0.000 claims 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims 1
FHEAIOHRHQGZPC-KIWGSFCNSA-N acetic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FHEAIOHRHQGZPC-KIWGSFCNSA-N 0.000 claims 1
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims 1
125000005529 alkyleneoxy group Chemical group 0.000 claims 1
125000005001 aminoaryl group Chemical group 0.000 claims 1
125000001769 aryl amino group Chemical group 0.000 claims 1
229940120638 avastin Drugs 0.000 claims 1
229960000397 bevacizumab Drugs 0.000 claims 1
229960001561 bleomycin Drugs 0.000 claims 1
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims 1
229960004117 capecitabine Drugs 0.000 claims 1
125000002837 carbocyclic group Chemical group 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
229960005243 carmustine Drugs 0.000 claims 1
ZDYYEIJLRMPBFE-WHSGIHJSSA-N chembl601445 Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2[C@H]3CC[C@H](CC3)OC)C2=N1 ZDYYEIJLRMPBFE-WHSGIHJSSA-N 0.000 claims 1
ZDYYEIJLRMPBFE-GOHCJOFJSA-N chembl602276 Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2[C@@H]3CC[C@H](CC3)OC)C2=N1 ZDYYEIJLRMPBFE-GOHCJOFJSA-N 0.000 claims 1
LQBQQAXIISEIGM-VCWRXUFXSA-N chembl606621 Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2[C@H]3CC[C@@H](O)CC3)C2=N1 LQBQQAXIISEIGM-VCWRXUFXSA-N 0.000 claims 1
LQBQQAXIISEIGM-RTWGARKQSA-N chembl610630 Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2[C@@H]3CC[C@@H](O)CC3)C2=N1 LQBQQAXIISEIGM-RTWGARKQSA-N 0.000 claims 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
229960004397 cyclophosphamide Drugs 0.000 claims 1
229960000684 cytarabine Drugs 0.000 claims 1
229960000640 dactinomycin Drugs 0.000 claims 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 1
229960000975 daunorubicin Drugs 0.000 claims 1
229960003668 docetaxel Drugs 0.000 claims 1
229960001904 epirubicin Drugs 0.000 claims 1
FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims 1
229960001842 estramustine Drugs 0.000 claims 1
229960002949 fluorouracil Drugs 0.000 claims 1
VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims 1
235000008191 folinic acid Nutrition 0.000 claims 1
239000011672 folinic acid Substances 0.000 claims 1
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
229960005277 gemcitabine Drugs 0.000 claims 1
229940045109 genistein Drugs 0.000 claims 1
TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 claims 1
235000006539 genistein Nutrition 0.000 claims 1
ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 claims 1
229960003776 glatiramer acetate Drugs 0.000 claims 1
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
MCAHMSDENAOJFZ-BVXDHVRPSA-N herbimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](OC)[C@@H](OC)C[C@H](C)[C@@H](OC)C2=CC(=O)C=C1C2=O MCAHMSDENAOJFZ-BVXDHVRPSA-N 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 claims 1
ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 claims 1
229960000930 hydroxyzine Drugs 0.000 claims 1
229960000908 idarubicin Drugs 0.000 claims 1
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
229960001101 ifosfamide Drugs 0.000 claims 1
229960003685 imatinib mesylate Drugs 0.000 claims 1
YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 claims 1
125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
229960004461 interferon beta-1a Drugs 0.000 claims 1
229960003161 interferon beta-1b Drugs 0.000 claims 1
229960004768 irinotecan Drugs 0.000 claims 1
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
229940043355 kinase inhibitor Drugs 0.000 claims 1
229960001691 leucovorin Drugs 0.000 claims 1
229960002247 lomustine Drugs 0.000 claims 1
229960004961 mechlorethamine Drugs 0.000 claims 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims 1
GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 1
229960001428 mercaptopurine Drugs 0.000 claims 1
229960000485 methotrexate Drugs 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
FCHXJPIEIHNGJM-UHFFFAOYSA-N methyl n-[4-[1-(1,4-dioxaspiro[4.5]decan-8-yl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCC4(CC3)OCCO4)C2=N1 FCHXJPIEIHNGJM-UHFFFAOYSA-N 0.000 claims 1
FTFGELDMGOAGIK-UHFFFAOYSA-N methyl n-[4-[1-ethyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound N1=C2N(CC)N=CC2=C(N2CC3CCC(O3)C2)N=C1C1=CC=C(NC(=O)OC)C=C1 FTFGELDMGOAGIK-UHFFFAOYSA-N 0.000 claims 1
SQJNNLMDYFXTSS-UHFFFAOYSA-N methyl n-[4-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C(C)C)C2=N1 SQJNNLMDYFXTSS-UHFFFAOYSA-N 0.000 claims 1
229960004857 mitomycin Drugs 0.000 claims 1
229960001156 mitoxantrone Drugs 0.000 claims 1
KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
LEFZXBFLARQTIC-UHFFFAOYSA-N n-[4-[[4-[1-methyl-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-6-yl]phenyl]carbamoylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=O)NC1=CC=C(C=2N=C3N(C)N=CC3=C(N3CC4CCC(O4)C3)N=2)C=C1 LEFZXBFLARQTIC-UHFFFAOYSA-N 0.000 claims 1
229960005027 natalizumab Drugs 0.000 claims 1
OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 claims 1
239000006186 oral dosage form Substances 0.000 claims 1
DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims 1
229960001756 oxaliplatin Drugs 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims 1
229960000624 procarbazine Drugs 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Chemical group 0.000 claims 1
229940063683 taxotere Drugs 0.000 claims 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims 1
229960001278 teniposide Drugs 0.000 claims 1
CEPZLSYRIXXARR-UHFFFAOYSA-N tert-butyl 4-[6-[4-(methylcarbamoylamino)phenyl]-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CC3CCC(O3)C2)=C(C=NN2C3CCN(CC3)C(=O)OC(C)(C)C)C2=N1 CEPZLSYRIXXARR-UHFFFAOYSA-N 0.000 claims 1
QXDYWHWVGFMFNY-UHFFFAOYSA-N tert-butyl 7-[6-[4-(pyridin-4-ylcarbamoylamino)phenyl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-4-yl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate Chemical compound C1C(O2)CN(C(=O)OC(C)(C)C)CC2CN1C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=NC=C1 QXDYWHWVGFMFNY-UHFFFAOYSA-N 0.000 claims 1
XCNFVVCWUVWYEG-UHFFFAOYSA-N tert-butyl 9-[6-[4-(2-hydroxyethoxycarbonylamino)phenyl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-4-yl]-3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC2COCC1N2C(C=1C=NN(CC(F)(F)F)C=1N=1)=NC=1C1=CC=C(NC(=O)OCCO)C=C1 XCNFVVCWUVWYEG-UHFFFAOYSA-N 0.000 claims 1
UBCOHNDNSCGERK-UHFFFAOYSA-N tert-butyl 9-[6-[4-(methylcarbamoylamino)phenyl]-1-(2,2,2-trifluoroethyl)pyrazolo[3,4-d]pyrimidin-4-yl]-3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2C3COCC2CN(C3)C(=O)OC(C)(C)C)=C(C=NN2CC(F)(F)F)C2=N1 UBCOHNDNSCGERK-UHFFFAOYSA-N 0.000 claims 1
229960003087 tioguanine Drugs 0.000 claims 1
MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims 1
229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
229960003048 vinblastine Drugs 0.000 claims 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims 1
229960004528 vincristine Drugs 0.000 claims 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 claims 1
229960002066 vinorelbine Drugs 0.000 claims 1
0 *C(C(*)OCC1O*)N1c1c(c(*)n[n]2*)c2nc(*I*)n1 Chemical compound *C(C(*)OCC1O*)N1c1c(c(*)n[n]2*)c2nc(*I*)n1 0.000 description 1

JP2010530074A 2007-10-16 2008-10-15 チエノピリミジンおよびピラゾロピリミジン化合物ならびにｍＴＯＲキナーゼおよびＰＩ３キナーゼ阻害剤としてのその使用 Withdrawn JP2011500702A (ja)